Method for the production of N-alkyl beta-hydroxylamine hydrocinnamonyl hydroxamic acids

Abstract

The subject invention is directed to a method of making compounds having the formula: ##STR1## wherein R 1 is alkyl, R 2 is H or alkyl, R 3 and R 4 are H, halogen, amino, alkylamino, alkoxy, alkyl, OH, O, NO 2 or combinations thereof, and X is CH or N, which compounds are useful as antihypertensive agents.

I claim: 
     
       1. A process for preparing N-alkyl beta-hydroxylamine derivatives of hydrocinnamonylhydroxamic acids which comprises contacting an alkyl cinnamate with N-alkyl-hydroxylamine and subsequently adding hydroxylamine thereto, the molar ratio of said hydroxylamine to said alkyl cinnamate being at least about 2:1. 
     
     
       2. The process of claim 1, wherein said N-alkyl-hydroxylamine is N-methyl hydroxylamine. 
     
     
       3. The process of claim 1, wherein the alkyl group of said N-alkyl-hydroxylamine contains from 1 to 7 carbon atoms. 
     
     
       4. The process of claim 1, wherein said N-alkylhydroxylamine is N-ethyl hydroxylamine. 
     
     
       5. The process of claim 1, wherein said N-alkylhydroxylamine is N-heptyl hydroxylamine. 
     
     
       6. The process of claim 1, wherein said alkyl cinnamate is ethyl cinnamate. 
     
     
       7. The process of claim 1, wherein the molar ratio of said hydroxylamine to said alkyl cinnamate is at least about 3:1. 
     
     
       8. The process of claim 1, wherein said hydroxylamine is added as an equimolar solution of hydroxylamine and an alkali hydroxide. 
     
     
       9. The process of claim 8, wherein said alkali hydroxide is potassium hydroxide.